Four Years
by Crittab
Summary: Jeff and Annie's first date. Rated M for romantic sexual situations.


**Title: **Four Years

**Disclaimer:** I don't own Community. I don't own anything. It's sad, really.

**Pairing:** Jeff/Annie

**Rating:** M/NC-17 for romantic sexual situations.

**Description:**Jeff and Annie's first date.

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**Four Years**

Four years. It had taken four years for Jeff to finally convince himself to ask Annie out. Four years of back and forth, multiple other relationships and endless desire, but finally they were on their first official date.

He knew why it had taken so long—he'd repeated his excuses to himself more times than he could count: she was too young; he wasn't good enough for her; she wanted a relationship, he didn't; she wanted romance, he was a dick; Shirley and Britta would castrate him... the list went on.

After four years of telling himself _no_, he finally changed his mind. Graduation was looming, Annie was a grown woman, and not even the very real threat of castration was enough to convince him anymore that she wasn't exactly who he wanted to be with. She was his best friend, and had been ever since they'd first met. They fought, they made up, they flirted and they teased. Annie hadn't made it a secret that she wanted more, and he was ready to give it to her. At 37 years old, Jeff Winger was finally ready to settle down.

When he picked her up, he couldn't help but smile at her outfit. Four years had matured his young friend, but it hadn't done anything for her fashion sense. That night he learned that Annie's 'date outfit' consisted of a slightly more sparkly cardigan, a slightly lower cut top, and a slightly nicer skirt. He was just thankful she'd traded in her classic ballet flats for a pair of pumps. Despite all of that though, he thought she looked beautiful. He told her so.

When they reached the restaurant, their food came quickly and they enjoyed friendly conversation as they eat. The whole scenario was very comfortable for them. Unlike many past bad dates, nothing seemed forced. After four years of friendship they could avoid the traditional perfunctory questions about families and jobs that first dates normally brought forth, and could just talk like 'them'. Like two friends who were excitedly moving forward in their relationship.

Jeff paid the bill about two hours after they had arrived. Neither felt rushed to get through the meal, or to make an exit. They were happy to sit and talk and be with their current company. It was exactly how a first date should be.

They made their way to Jeff's car where he held the door for her. She smiled at the gesture and slid in, buckling as he climbed in on the driver's side and started the ignition.

"So, where to now, Jeeves?" Annie asked with a grin. Jeff laughed.

"I could take you home," he replied. She shrugged.

"I'm not really ready for the evening to end." He smiled at this.

"Neither am I."

"So, coffee?" she asked. "At your place?" He nodded slowly, relieved that it had been her idea.

"Coffee sounds good." She smiled widely as he pulled the car out of the space and began their ride back to his apartment. The ride was rather quiet, but not at all awkward. Jeff took Annie's hand and they sunk into a comfortable silence as the street lights whizzed by.

When they finally arrived back at Jeff's apartment, he opened her door and helped her out of the car, and then held the door for her as they entered the building.

"You're quite the gentlemen when you're on a date," Annie said with a grin when they reached his apartment. Jeff smiled and headed into the kitchen to make the coffee while Annie settled into one of the bar stools that lined the kitchen counter.

"Well, it's either that or never stand a chance of have a lasting relationship."

"This coming from the guy who has had three relationships in his life, two of which lasted less than four months."

"Hey, I never said I had one, I'm just saying it keeps the possibility of having one open," he said with a grin, pouring her a cup of the hot liquid. She took a long sip from the cup as he came around the counter, sitting next to her.

"Have I told you yet how beautiful you look tonight?" he asked, putting his hand on her knee. She smiled widely and set down her cup, resting her hand on top of his.

"A few times, but you're welcome to continue." Jeff just smiled and looked down at their hands.

"This is nice," he said in a low voice. She nodded.

"Yea, it is," she agreed. A comfortable silence fell between them. After a moment Annie stood up and walked closer to Jeff so she was standing in between his legs. He smiled lightly and wrapped his arms around her waist, pulling her closer.

"So it may not be proper 'first date' etiquette, but since we've already kissed a few times, I don't think there would be a problem if I kissed you now. Do you?" she asked. He just smiled and leaned into her, catching her mouth with his own in a slow, exploring kiss.

Slowly, Annie allowed herself to sink into him, wrapping her arms around his neck as his tightened around her waist. She opened her mouth slightly, allowing him to explore it with his tongue. When it first entered her mouth she fought not to smile at the feeling of having part of Jeff enter part of her. She slowly ran her tongue along his, tasting it, learning it, enjoying it.

She allowed one of her hands to graze down his spine and then back up, entangling it in his hair, while his hands began to explore her back. Slowly he pushed her away, stood, and then captured her lips again, pinning her against the counter. She smiled against his lips.

"So I guess I'll take that to mean you don't mind?" she asked in a low voice. He raised his eyebrow.

"What are you talking about?" he asked, all conversation leading up to this point forgotten. She just grinned.

"Never mind," she said softly, kissing him again, slowly and sweetly, before taking his hand and leading him to through the darkened apartment into his bedroom.

When they came through the door, Jeff closed it behind them and turned back to Annie, who was standing a few feet away from him, her hands clasped in front of her.

"Soo..." she said slowly. Jeff chuckled, nervous, but excited at the same time.

"So," he mimicked. She smiled and took a few tentative steps toward him, feeling butterflies taking flight in her stomach. The room was dark, but neither made a move to turn on the light. The soft glow from the street lamps outside cast a comfortable, dim light throughout the room, making everything visible but hazy.

Jeff closed the distance between them, putting on hand on her hip and the other on her cheek, leaning down and catching her lips in a slow, easy kiss. She unclasped her hands and wound them through his arms and around his midsection, pulling him close. Slowly she pulled away from the kiss and smiled up at him, the light from outside catching his blue eyes and making them sparkle.

"This isn't weird," she said softly. He laughed lightly.

"Not really," he shrugged. "But this being you and me, it doesn't really seem like it should be." She sighed and allowed herself to sink into his embrace as he held her close. He held her for a moment, just enjoying the feeling, not wanting to rush anything. Slowly she pulled away from him, slipping off her cardigan and letting it fall to the floor.

Slowly he leaned back in, catching her lips softly, comfortably. She wrapped her arms around his neck as he put his around her midsection, pulling her against him. She could feel his erection growing slightly in his pants, which aroused her even more than she already had been.

He allowed his hands to begin roaming over her back, grazing them up and down her spine all the way down to her backside and then back up. She enjoyed the feeling of his large hands exploring her, and leaned into him, urging him to continue. Slowly she brought her hands around to his front, never breaking the kiss, and began to undo each button of his shirt ever so carefully, not wanting to rush the moment. She pulled his shirt out from his pants and pushed it off his shoulders, pulling away from the kiss as he shrugged it off.

She took his hand in hers and silently led him toward the bed, sitting him down as she stood before him. He slowly ran his hands up her sides from her thighs, along her hips, and up to the sides of her breasts before tugging on the hem of her shirt and pulling it over her head, discarding it gingerly on the floor. She smiled and leaned down, kissing him softly and pushing him down on to the bed, as she followed him down, laying on top of him.

He ran his hands along the length of her back and down to her legs and then back up, enjoying the feeling of her body over his. Their kisses remained sweet and slow, neither feeling it necessary to rush the moment. She pulled away slightly and sat up so she was straddling him, reaching down she tugged at the hem of his undershirt. He sat up so she could pull it over her head, and then caught her mouth in a heated kiss, pulling her closer to him so he could feel her skin against his.

She opened her mouth to allow him entrance, now familiar with his tongue, as they began to fight for dominance over the kiss, tongues duelling neither wanting to break the searing embrace. With Annie still straddling him, Jeff stood up and turned them around, easing her down onto the bed and following suit. He hovered above her and began to kiss her neck, which she arched to allow him better access. He eased his knee in between her legs, pressing it flush against her as he continued to kiss her.

She laughed lightly as he caught her ticklish spot on her neck. Noticing the reaction he chuckled and began to place feather-light kisses over the area, resulting in giggles from her.

"You're tickling me," she said through her laughter. He just grinned and continued along with his explorations. Putting his weight onto his left arm, he began to graze his right hand along her chest and then down through the valley between her breasts, along her stomach upon which goose bumps were rising from his touch, and down to the clasp on her skirt, which he undid carefully before slowly pulling down the zipper. He pulled away from her completely, standing and slowly pulling her skirt down her legs, tossing it away. She sat up and set to work on his pants, allowing them to join their other clothes on the floor before pulling him back down to her.

Slowly they inched their way into the center of the bed, laying next to one another. They grazed their hands over each other, taking time to learn every inch of their bodies.

He explored her body with his hands, running his fingertips along her arm, and entwining their fingers, bringing her hand to his mouth, kissing the tip of each finger lightly, and her palm, and then the veins on her wrist before continuing his exploration. She smiled at his unexpected tenderness.

"I like this," she said with a wide smile. He returned the smile and kissed her lightly.

"Me too," he agreed. She smiled at him and took hold of his hand and kissed his palm softly, before placing it lightly atop her breast. Jeff was a little surprised by this, not expecting her to be so assertive, but he slowly recovered as he allowed his thumb to make little circles over the skin that was exposed above the material of her bra. He leaned down and kissed the skin that he had just been exploring as he reached around behind her and unclasped the bra. He leaned back and looked in her eyes, as if asking for permission to remove the material. She just smiled at him, and he slowly pulled each strap from her shoulders and pulled it away, exposing her for the first time to him.

He readjusted them slightly, settling on top of her and putting his weight on his arms. He leaned down and kissed her lips in a long, sweet, promising kiss before kissing his way down her neck, and along her chest, before coming to settle over her left breast.

He kissed the mound of flesh for a few seconds before licking lightly at her nipple and taking it into his mouth. He swirled his tongue around the nub, enjoying the way her breathing became more shallow in response to his ministrations.

She rested her head back into the soft pillows and closed her eyes, revelling in the feeling of Jeff's warm mouth on her as his other hand rubbed along her other breast, grazing his palm over her nipple and then rubbing it under his thumb.

After a while, Jeff switched his attention to her other breast, providing it the same treatment, slowly eliciting quiet moans, happy with the knowledge that it was finally him who could elicit such sounds from Annie. Slowly he began to place light kisses along her stomach, heading downward ever so slowly.

He slipped his fingers under the material of her panties, pulling them down just a little bit so he could kiss the newly exposed flesh. This caused Annie to moan, as she lifted her hips lightly, urging him to pull off the offending material, finally. He smirked, pleased with her reactions, and continued his slow torture, eliciting a whine from Annie.

"Jeff," she said breathily. He raised his head to look at her, a gleam in his eye. She rolled her eyes. "Take it off," she demanded. He just laughed, as he continued to explore the soft skin inch by inch until he had removed the garment entirely. He sat up and took her in, her first time completely exposed to him. It left him breathless.

"You're beautiful," he said hoarsely. She smiled and reached for him, to which he obliged and laid down on top of her, kissing her fully as her hands wandered down his body, tugging at the waistband of his boxers. He pulled away and removed the final garment that stood between them before returning to his position above her, laying flush against her, both revelling in the feeling of the skin on skin contact they had each been dying to feel.

"I want to feel you," she whispered to him. He took in a breath and leaned down, kissing her lightly.

"You sure?" he asked. He'd never asked before, but he never wanted to make Annie feel uncertain about him. He was relieved when she smiled brightly and nodded her consent. He reached over to his bedside table and pulled out a condom, putting it on, and settling on top of her again. He kissed her deeply and passionately, letting go of his inhibitions in this moment, and just allowing her to know how desperately her wanted her.

She spread her legs apart, allowing him to settle in between them. Slowly she reached down and took hold of his erection for the first time, pumping it a few times causing him to breathe in quickly at the new sensation of being held by her. Slowly she positioned him at her entrance, looking in his clear blue eyes, and smiling. Jeff smiled back and leaned down, kissing her softly before slowly pushing himself into her, a moan escaping both of their lips as he did.

Once fully inside, both felt a rush of excitement course through their veins. He waited a moment for her to adjust to his size inside of her.

"Wow," she whispered. He laughed lightly. She pulled him to her, kissing him fully before pushing her hips against his, urging him to continue.

Slowly he pulled out about halfway before pushing in again. Ever move was deliberate, each bringing a new wave of excitement to both of them. He pulled out again, a little more than the last time, pushing back in a little faster.

They continued on like this, kissing, tasting and learning each other as they moved together, building an intensity and heat between them.

"Faster," Annie demanded in a hoarse whisper. Jeff obliged and sped up slightly, still maintaining a steady rhythm, which brought Annie to new heights of anticipation and desire.

As the moments wore on, they continued to move together, faster, harder, more demanding. Jeff began to move quickly inside of her, feeling pleasure build and course through his body. She was so slick, so ready, and felt so perfect.

Annie rolled her head back against the pillows, opening her mouth and moaning Jeff's name as the pleasure consumed her. She could feel her orgasm build and build until she felt explosions happening within her. She bucked against him multiple times as she reached her peak, causing his to come not long after.

As his orgasm came he plunged into her over and over, grunting in pleasure as he came.

As the pulses of pleasure finally began to subside he pulled out of her, and came to rest on top of her, both breathing hard and holding tightly to the other's hot, slick body. He buried his head in her neck, catching his breath and kissing the soft flesh there gingerly.

Hesitantly, he pulled away from her, coming to rest at her side. He discarded the condom in a waste basket before relaxing next to her with a smile on his face.

She rest against him, tired, but exhilarated. She took his hand in hers and began to trace her finger along his palm, a satisfied smile finding its way to her lips.

"Wow," she whispered. He chuckled lightly.

"Wow," he replied. She smiled up at him, meeting his eyes. He leaned in slowly for a kiss. When she pulled away she rested against him again, taking his hand back to play with, not wanting to end contact with him.

"I don't know why we waited four years to do that," she mumbled into his chest. He smiled lightly and placed a lingering kiss to her forehead. Together, they sunk into the pillows and closed their eyes.

"Neither do I."

Together, they fell into a contented, companionable silence before drifting off to sleep.

**End**

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_**A/N:** Okay, confession time—I originally wrote this fic for another couple on another show, but it just screamed Jeff/Annie to me, so I reworked it. Hope you liked it! _


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